Fentanyl

Base Information

• Chemical Name: Fentanyl
• CAS No.: 437-38-7
• Deprecated CAS: 80832-90-2
• Molecular Formula: C22H28N2O
• Molecular Weight: 336.477
• Hs Code.: 2933330000
• European Community (EC) Number: 207-113-6
• UNII: UF599785JZ
• DSSTox Substance ID: DTXSID9023049
• Nikkaji Number: J5.736C
• Wikipedia: Fentanyl
• Wikidata: Q407541
• NCI Thesaurus Code: C494
• RXCUI: 4337
• Pharos Ligand ID: 4ZQJCPWP7BNN
• Metabolomics Workbench ID: 43104
• ChEMBL ID: CHEMBL596
• Mol file: 437-38-7.mol

Synonyms:Duragesic;Durogesic;Fentanest;Fentanyl;Fentanyl Citrate;Fentora;Phentanyl;R 4263;R-4263;R4263;Sublimaze;Transmucosal Oral Fentanyl Citrate

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Chemical Property of Fentanyl

Chemical Property:

• Appearance/Colour: Pale brown solid
• Melting Point: 83-84 °C
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 466.2 °C at 760 mmHg
• PKA: 8.4(at 25℃)
• Flash Point: 185.8 °C
• PSA: 23.55000
• Density: 1.087 g/cm³
• LogP: 4.07460
• Storage Temp.: Controlled Substance, -20°C Freezer
• Solubility.: Practically insoluble in water, freely soluble in ethanol (96 per cent) and in methanol
• Water Solubility.: 0.2g/L(25 oC)
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 336.220163521
• Heavy Atom Count: 25
• Complexity: 391

Purity/Quality:

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/25-36/38-39/23/24/25-23/24/25
• Safety Statements: 16-24-45-36/37-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
• Recent ClinicalTrials: Comparison of Patient-controlled Analgesia Regimenfor Postoperative Pain in Patients Undergoing Total Knee Arthroplasty
• Recent EU Clinical Trials: PAIN CONTROL WITH THE USE OF WALANT IN TOTAL TRAPEZECTOMY. RANDOMIZED CLINICAL TRIAL
• Recent NIPH Clinical Trials: midazolam / fentanyl combined in EBUS-TBNA
• Uses: Used as an analgesic. Controlled Substance Fentanyl is available in a variety of preparations for parenteral, transdermal and transmucosal (including buccal) administration. Because of high firstpass metabolism (~70%) it is not given orally. It is approximately 80–100 times more potent than morphine in the acute seing, although it is approximately 30–40 times as potent when given chronically (e.g. slowrelease transdermal patches). With transdermal administration, the patch and underlying dermis act as a reservoir, and plasma concentration does not reach steady state until approximately 15h after initial application. Plasma concentration also declines slowly after removal (t1/2 ~15–20 h). Fentanyl is very lipophilic, with a relatively short duration of action. There are several new buccal/transmucosal preparations developed for rapid-onset breakthrough pain. These aim to have a very rapid onset in approximately 10min, although this may not be the case in clinical practice. Fentanyl has a large VD with rapid peripheral tissue uptake, limiting initial hepatic metabolism. This may result in significant variability in plasma concentrations and secondary plasma peaks. It binds to αl-acid glycoprotein and albumin; 40% of the protein-bound fraction is taken up by erythrocytes. The lungs may be important in exerting a first-pass effect on fentanyl (up to 75% of the dose), thus buffering the plasma from high peak drug concentrations.
• Therapeutic Function: Narcotic analgesic
• Clinical Use: Fentanyl (Sublimaze) and its related phenylpiperidine derivatives are extremely potent drugs.They are used as adjuncts to anesthesia, and fentanyl may be given transdermally as an analgesic and as an oral lozenge for the induction of anesthesia, especially in children who may become anxious if given IV anesthesia. Fentanyl is 80 to 100 times as potent as morphine. Sufentanil (Sufenta) is 500- to 1,000-fold more potent than morphine, while alfentanil (Alfenta) is approximately 20 times more potent than morphine. Their onset of action is usually less than 20 minutes after administration. Dosage is determined by the lean body mass of the patient, since the drugs are lipophilic and tend to get trapped in body fat, which acts as a reservoir, prolonging their half-life. In addition, redistribution of the drugs from the brain to fat stores leads to a rapid offset of action. Droperidol, a neuroleptic agent, is generally administered in combination with fentanyl for IV anesthesia. Fentanyl transdermal patches are available for analgesia in chronic pain and for postsurgical patients. The use of the patch is contraindicated, however, for patients immediately after surgery because of the profound respiratory depression associated with its use. The patches must be removed and replaced every 3 days. The onset of action of transdermal fentanyl is slower than that of oral morphine. Thus, patients may require the use of oral analgesics until therapeutic levels of fentanyl are achieved. Fentanyl lozenges have been used to induce anesthesia in children and to reduce pain associated with diagnostic tests or cancer in adult patients. However, all of the adverse side effects associated with morphine are produced with far greater intensity, but shorter duration, by fentanyl in the patch, the lozenge, or IV administration. Given the abuse liability of fentanyl, controversy exists as to the ethics of marketing a lollipop lozenge form. Sufentanil is much more potent than fentanyl and is indicated specifically for long neurosurgical procedures. In such patients, sufentanil maintains anesthesia over a long period when myocardial and cerebral oxygen balance are critical.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: metabolism increased by rifampicin. Antidepressants: possible CNS excitation or depression (hypertension or hypotension) in patients also receiving MAOIs (including moclobemide) - avoid concomitant use; possibly increased sedative effects with tricyclics. Antifungals: concentration increased by triazoles. Antihistamines: increased sedative effects with sedating antihistamines. Antipsychotics: enhanced hypotensive and sedative effects. Antivirals: concentration increased by ritonavir; increased risk of ventricular arrhythmias with saquinavir - avoid. Cytotoxics: use crizotinib with caution. Dopaminergics: avoid with selegiline. Sodium oxybate: enhanced effect of sodium oxybate - avoid concomitant use

Technology Process of Fentanyl

There total 25 articles about Fentanyl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

ethene (74-85-1) + carbon monoxide (201230-82-2) + (1-Phenethyl-piperidin-4-yl)-phenyl-amine (21409-26-7) → N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide (437-38-7)

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); hydroxylamine hydrochloride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; at 120 ℃; for 24h; Autoclave; High pressure;

DOI:10.1016/j.tetlet.2015.12.031

Reference yield: 95.0%

propionyl chloride (79-03-8) + (1-Phenethyl-piperidin-4-yl)-phenyl-amine (21409-26-7) → N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide (437-38-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 2h; Reagent/catalyst; Solvent;

DOI:10.1371/journal.pone.0108250

Reference yield: 94.0%

fentanyl citrate (1863-07-6,990-73-8) → N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide (437-38-7)

Guidance literature:

With sodium hydrogencarbonate; In water;

upstream raw materials:

(1-Phenethyl-piperidin-4-yl)-phenyl-amine

propionic acid anhydride

propionyl chloride

1-(2-phenylethyl)-4-piperidinone

Downstream raw materials:

fentanyl hydrochloride

N-([2-⁽²⁾H]-1-(2-phenylethyl)-4-piperidinyl)aniline

C₂₂H₂₇⁽²⁾HN₂O

fentanyl citrate

Refernces

• 1、 Kanamori, Tatsuyuki,Okada, Yuki,Segawa, Hiroki,Yamamuro, Tadashi,Kuwayama, Kenji,Tsujikawa, Kenji,Iwata, Yuko Togawa. "Evaluation of agonistic activity of fluorinated and nonfluorinated fentanyl analogs on μ-opioid receptor using a cell-based assay system". . p. 159 - 161. Retrieved 2021/02/09.
• 2、 Walz, Andrew J.,Hsu, Fu-Lian. "An Operationally Simple Synthesis of Fentanyl Citrate". . p. 467 - 470. Retrieved 2017/10/06.